The maritime supply chain is a colossal ecosystem and the interface of the intercontinental trade market. Within this ecosystem, freight transportation is considered a fundamental component of all supply chain systems. As a matter of its demanding multimodal and intermodal character, freight transportation is a highly competitive market where actors involved, demand reliable and high-quality services at competitive prices. However, even though its systems keep evolving, being spurred by developments at multiple levels, the maritime actors’ fundamental operational processes keep an unprecedented low pace of evolution and transformation, and the maritime supply chain market is considered to be as hyper-fragmented as ever. This paper investigates how the effective, efficient, and sustainable matching of the demand and supply needs of the actors involved in the maritime supply chain domain can be strategically achieved and supported through specialised information systems. The paper, also presents a holistic framework for designing these systems. The analysis was based on the outcomes received from a number of interviews conducted with strategically positioned experts, pointing out their emerging needs and the challenges they face. The outcomes showed that digital transformation is still in its infancy but that the embracement of a decision-matchmaking system could be a real game changer.